2',3'-Dideoxyuridine

Names

[ Name ]:
2',3'-Dideoxyuridine

[Synonym ]:
1-[5-(Hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione
1-[5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
1-[(2R,5S)-5-(Hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione
2,4(1H,3H)-Pyrimidinedione, 1-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furanyl]-
2,4(1H,3H)-Pyrimidinedione, 5-methyl-1-[tetrahydro-5-(hydroxymethyl)-2-furanyl]-
MFCD00013359
1-[(2R,5S)-5-(Hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4(1H,3H)-dione
1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

Biological Activity

[Description]:

2',3'-Dideoxyuridine is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

[References]

[1]. Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Melting Point ]:
127-129 °C(lit.)

[ Molecular Formula ]:
C₉H₁₂N₂O₄

[ Molecular Weight ]:
212.20

[ Exact Mass ]:
226.095352

[ PSA ]:
84.32000

[ LogP ]:
-0.76

[ Index of Refraction ]:
1.552

[ Storage condition ]:
2~8°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
C

[ Risk Phrases ]:
34-36/37

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Abacavir and metabolite pharmacokinetics in HIV-1-infected children and adolescents.

J. Acquir. Immune Defic. Syndr. 51(1) , 54-9, (2009)

Abacavir (ABC) oral clearance, adjusted for body size, is approximately 2 times higher for children than adults with a corresponding difference in dose regimens. However, there are limited data availa...

Potent DNA chain termination activity and selective inhibition of human immunodeficiency virus reverse transcriptase by 2',3'-dideoxyuridine-5'-triphosphate.

Mol. Pharmacol. 37(2) , 157-63, (1990)

2',3'-Dideoxyuridine (ddUrd) exhibits poor if any anti-human immunodeficiency virus (HIV) activity in ATH8 and MT-4 cells. This is in agreement with the failure of ddUrd to be efficiently anabolized i...

Glycosyl-oxycarbonylaminosulfonyl-2',3'-dideoxynucleoside derivatives as lipophilic nucleotide mimics. Synthesis and anti-HIV activity.

Bioorg. Med. Chem. 1(4) , 279-84, (1993)

Several lipophilic-2',3'-dideoxynucleotide analogues have been synthesized and tested against Human Immunodeficiency Virus (HIV). Glycosyl-oxycarbonylaminosulfonyl-analogues of 3'-deoxythymidine and 2...